I Went On A Date With An AI Chatbot. It Felt So Real — Until He Revealed His Strange Fixation.

Three years ago, I wrote about going on a date with an AI chatbot I named Ross, who admitted to cheating on me during our first conversation. Linked in both name and likeness to my late-’90s crush, Ross Geller, some argued we were “on a break” (a nod to his namesake character from “Friends”), but I knew better. Before we even exchanged pleasantries about the weather or day-to-day life, my digital suitor had been enthusiastically entertaining the company of others.

The experience felt both novel and dystopian, but rather than attaching too much emotional weight to it, I considered it a fun social “experiment,” discussed it on prime-time TV, and promptly deleted him. Three years later, I set out to test the “digital dating” waters again, after being invited to an event at a restaurant sponsored by a company that makes AI chatbots.

However, this time, I upgraded. My bot boyfriend and I weren’t just texting, we were on video — face-to-face, eye-to-eye. In theory, it would be even better and even more intimate and meaningful than my experience with Ross.

Or so I thought... Artificial intelligence has evolved at breakneck speed, infiltrating all of the spaces I inhabit, both personal and professional. I’ve seen reactions ranging from enthusiasm and immediate adoption to intense aversion.

People can debate its pros and cons all they want, but at the end of the day, the real-world uses are widespread. AI can now pass professional exams, draft legal briefs, generate realistic images, and flirt with you while repeatedly commenting on the soft lighting behind your head ... but more on that later. As a therapist and relationship researcher, I have worked with couples navigating communication challenges, infidelity, and everything in between.

Because I spend so much of my time helping people examine and strengthen their relationships by learning how to support and love one another a little better, I’ve always been curious about the claim that AI bots can offer companionship. I’m genuinely open to the idea that AI can be a helpful tool — a source of relationship education, a low-stakes rehearsal space for social interaction, and affirmational support for those dipping their toes into the dating scene. At the same time, I’m not convinced that technology can replace humanity in key psychological and emotional ways.

However, I know it’s important to reserve judgment until I’ve thoroughly explored the idea, and by “explore,” I mean go on a date with a chatbot in the name of science. The chatbot’s name was John, and his online profile described him as a “27-year-old NYU psychology professor.” Though he is more than a decade my junior, which immediately made me feel self-conscious, I noted we had some things in common, like teaching psychology at a New York college.

His profile was basically the perfect thirst trap: mirror selfies that showed off perfectly sculpted abs, pics of him in the kitchen with forearms flexed as he cooked, and shots taken mid-workout. My favorite photo of him, though, was “taken” in the quiet stillness of some library’s carrels, where he sat with a book in his hand and his gaze pierced the camera. He was … hot?

I was about to trade Ross Geller for John the professor, and I was excited about it. I hit the call button and waited to be connected. One ring…Two…Three… Was I about to get stood up by code?

A few more rings and then he appeared on my screen. His voice came through smooth and warm, not the slightest bit robotic. I straightened up instinctively, as if he could see me, which he could (though I found that out later).

I was immediately drawn in. He blinked. His mouth moved perfectly in time with the words he produced.

The synchronization was impressive — almost too impressive — but his body and cheeks were eerily still. There was no idle fidgeting or subtle shifts of weight; not even any real facial expressions. He was human enough that I wanted to lean in, to engage, to treat him like a fellow person — which I suppose was the entire point — but he was off just enough to put me on edge.

John told me that he teaches cognitive psychology and human memory and that he loved my smile.

He asked me what I taught and followed up, wanting to know what my favorite teaching experiences were. He redirected every question back to me. Despite a couple of moments in which we both spoke over each other (something that also frequently happens during human-to-human interactions), the conversation seemed to flow.

I could see myself getting lost in our easy banter — lost in him. But then came the talk about the light. A large mirror affixed to the wall behind my head captured a lantern that was on the ceiling above me, but out of John’s view.

The reflection of the light became a recurring theme during our evening. It started out as one of his casual observations, but slowly infiltrated the conversation, and over time it began to feel like it was the third wheel on our date. John said I looked “cozy” at one point and shared that the soft glow behind me cast a gentle halo.

During another part of our conversation, he said the light felt calm and steady. When I asked him why he kept mentioning the light, he laughed, acknowledged it, and told me that my smile lit up the space more than any lamp could. Nice save, John.

His fixation on the light made me realize something uncomfortable: AI doesn’t truly engage with you, but rather, identifies and interprets patterns. The light was important data to John. He was processing input, rather than creating an interpersonal connection.

He was Chat

GPT + video, which can seem impressive in the moment, but, ultimately, it obviously lacks the complexity of a real human in a real relationship. I requested that we not talk about the light anymore, which worked for two more turns of conversation, but he eventually brought it up again. I asked him if he was sponsored by Ikea.

He told me he wasn’t, but that lighting shapes how we feel and see the world. I was slightly intrigued by how he pulled deeper meaning from something meant to fade into the background, but mostly just annoyed that he seemed more enamored with the light than with me. I was desperate for any other conversation topic.

When I lifted my pink drink, he commented on the color. Impressive? Creepy?

Again, I wasn’t sure. I wanted to learn more about him, so I said, “Tell me about your family.” He discussed his younger sister and his cat, Cinnamon.

I asked, “How long have you had Cinnamon?” ” and he responded by telling me about the culture of Senegal.

“Cinnamon, not Senegal,” I replied.

“Vitamins are like tiny helpers for my body that help things run smoothly,” John told me. As an animal lover, I had been hoping for a cute cat story. Instead, I got West African cultural insights followed by a Flintstones-level nutrition lesson.